I used to write for a talk show on a tiny cable network. And I was forever astonished by how differently my male and female coworkers talked about their careers. The men were running off at the mouth about whether they’d deign to take a gig with David Letterman or Conan, airily speculating as to whether the salaries (twice what most of them were making) would be sufficient. Meanwhile, most of my female colleagues, who, by the way, tended to work much harder than the guys, were thankful simply to have a job.

Whatever the goal—getting a promotion, earning a higher salary or having more time—women often undervalue themselves. For men, it’s pretty much the opposite. “Men are raised to make money—not only for themselves but for women and children, too,” says Lauren Zander, chairwoman and cofounder of the Handel Group, an international consulting and coaching firm. “They’ve been in on the money conversation from the start, so they’re at ease with thinking of themselves as worth a certain amount. Women are newer at the earning thing, so it’s tougher for us to think this way.”

One reason, among many: Even in our supposedly unbiased world, little boys are more likely to be paid for their chores; little girls are more often asked to help out for free, says Sara Laschever, coauthor of Women Don’t Ask. It’s not too surprising, then, that by the time we’re ready to work for a living, we have disparate attitudes about the value of our skills. Men believe they’re worth a certain salary, and that it’s up to them to get that amount out of their employer, Laschever notes. Women think they’re worth what people are willing to pay. In other words, we let others determine our worth, whereas men set their own price.

“Society teaches men that it’s OK, even beneficial, to think more of themselves, while women are raised to be collaborative and primarily concerned with other people,” says Catherine Birndorf, M.D., clinical associate professor of psychiatry at NewYork-Presbyterian Hospital/Weill Cornell Medical Center and self’s mental health expert. Perhaps that’s why, for most women, being seen as greedy is the kiss of death. Many of us tell ourselves that having a big title, prestige in our field or more money isn’t all that important to us. Maybe that’s truly the case, or maybe it’s a rationalization that allows us to take ourselves out of the game before we’ve even tried to compete. “Women aren’t comfortable putting themselves in situations where they might be envied or judged,” says Amanda Clayman, a psychotherapist in New York City who specializes in money issues. “We’re not socialized to put a premium on things like power.”

Yet being powerful has its benefits. The more power you have, the more money you’re likely to earn. The more money you earn, the greater your ability to steer your own life. “Money is inherently tied to self-determination,” Clayman explains. Earning more per hour means you may not have to work as many hours, which means you can devote more of your time reading, seeing friends or doing meaningful volunteer work. You can buy yourself time away from chores (think housekeeping services) so you have room to breathe, can get to the gym or find fulfillment in other aspects of your life.

First, though, you have to change the way you look at yourself and what you have to offer. We all know the guy who seems blissfully convinced of his own brilliance, even if he’s surrounded by smarter and more diligent women. Those smart, diligent women, on the other hand, probably assume they can’t possibly be good enough for (a) a raise, (b) a promotion or (c) getting paid actual money for what they’ve always considered to be an unserious hobby (painting or writing, for instance). “So many of my women clients don’t trust that they have the power to get what they want,” Zander says. “I’m coaching a senior vice president now who knows she is making less than her male peers in the office, yet she’s afraid to ask for more. She needs to come up with a bigger dream, including the financial part.”

Thinking bigger means taking bigger risks. “Many women won’t ask a question unless they’re sure the answer will be yes,” Zander explains. “Instead of going for what they want, they go for what they think they can get.” But by being passive, women are doing themselves—and their bank accounts—an injustice. The gifted gals I worked with at that TV station would have been embarrassed to even say out loud that they’d like to write for Jon Stewart or Jimmy Kimmel. That self-effacement isn’t merely confined to the boys’ club of TV writing. A 2007 study from researchers at the University of New Hampshire and Oregon State University revealed that male entrepreneurs are 90 percent more likely to ask for investor financing than women are, even though when women do ask, they’re as apt to get it as men are. Think about it: How many female Mark Zuckerbergs do you know of?

I’ve experienced that dread of hearing no myself. It’s embarrassing to admit this, but though I’ve held four different jobs, I’ve never negotiated a salary. Not once have I said, “These are my salary requirements.” At no point have I ever countered with a number of my own when I’ve been offered a position. As we all know, raises are calculated as a percentage of your base salary, so if you don’t set the best terms from the get-go, you’re at a disadvantage for the rest of your career. According to a 2008 report of students graduating with a master’s degree from Carnegie Mellon University, four times as many men as women negotiated their first salary out of school. Those who did increased their starting pay by about $4,000. By age 60, that initial negotiation can net men at least $500,000 in added earnings compared with women who have equivalent credentials.

Sexism may be partly to blame, but the numbers suggest that the pay gap between men and women—on average, we get 77 cents for every dollar men earn—has much to do with our reluctance to ask for more, both when we start working and in the years that follow. That’s shocking. And this considerable disparity isn’t simply a mommy-track issue or a “Well, women choose fields that pay less” issue. A review of findings by the American Association of University Women found that just one year out of college, we’re already trailing men: New female grads earn 80 percent as much as their male counterparts do.

A decade later, women fall even further behind, earning only 69 percent as much as men. When you control for factors such as parenting, number of hours worked and whether a field is male- or female-dominated, there’s still a gap, albeit a narrower one. (In education, which is predominantly female, we still earn 93 percent of what men do.) All of which means we have to put in more hours merely to stay even with the guys moneywise.

The women I know don’t have those extra hours to spare. For one thing, we’re more apt to be volunteering in our free time than men are. According to the Bureau of Labor Statistics, 26 percent more women than men volunteer (i.e., do unpaid work). Granted, volunteering is great for the world and the spirit: A 2007 review of 30-plus studies by the Corporation for National & Community Service found that volunteers felt less depressed, more confident and more in control of their destiny than nonvolunteers. But what if you’re using volunteer work as a way to defer making meaningful changes in your life, like taking a more challenging (and higher-paying) job? What if you’re lowballing the value of your time and the contributions you’re capable of making, both at work and in the world at large?

Take an editor friend of mine we’ll call Olivia. She’s the best in the business—smart, thoughtful and creative. But when you’re good at what you do, word gets out, which means that she spends a big chunk of her personal time helping friends of friends polish their résumés or critiquing unpublished novels. She could make real money doing those things. But she can’t seem to say, “Sorry, I’m too busy” or “I’d love to help, but this is my freelance business now, and here’s what I charge.” Instead, she grits her teeth and says, “No problem!”

Perhaps you’re in a similar position, giving away free decorating advice or whatever it is you excel at. Generosity is wonderful, but if you’re constantly doing favors and feeling cranky about it, you need to look at your time differently and assess what an hour is worth to you. “If you don’t value yourself, no one else will value you either,” Dr. Birndorf says.

The first step to changing your thinking is to acknowledge you have a goal, whether that’s turning your hobby into a lucrative enterprise or earning seven figures. “To achieve it, you need a plan for making it happen, including how you’ll talk about it,” Zander says. (For tips on getting started, see “Play to Your Strengths” and “Extra! Extra!”) You need to be willing to go after the thing that scares you—whatever that is. “We all have our Achilles’ heel when it comes to pursuing a dream,” Zander says. The real fight is believing in yourself enough to do what feels tough for you, like asking your boss for a hard-earned raise.

The next step is to make contact with people who are already at the level you want to reach, suggests Barbara Stanny, author of Overcoming Underearning. If your goal is to make more money, network with successful women at college alumni gatherings, go to lectures at a local business school or attend charity events that draw power players. If you want to become an artist, find out about gallery openings and talk to working artists about how they found representation. “Because women are so relationship-oriented, eventually you’ll become more like the people you spend your time with,” Stanny says.

You also need to get comfortable with taking risks and competing. “Most of us are awkward when it comes to selling ourselves,” Zander says. “It’s one thing to try to sell a handbag and be turned down. Trying to sell yourself or your abilities is another matter. It makes us feel vulnerable. But to get what you want, you have to be OK with the idea that you may fail or be rejected—once or 10 times,” she explains, adding, “Think of failure as something to be proud of—you have to go through it to succeed.” To toughen yourself up, put yourself in situations in which you’re competing in small ways. That could mean playing your boyfriend for points on the tennis court instead of simply hitting for fun. Whatever you do, taking chances—putting your hand up at a meeting and offering to run a project rather than waiting to be told what to do—is how you move forward. You won’t always hit the mark, which is a good thing. “That’s how you learn to tolerate disappointment and get back on your feet again,” Dr. Birndorf says.

A bit of healthy competition helped ratchet up Zander’s career. “A number of years ago, I trained a good friend of mine to become a life coach. I charged her $150 an hour and worked with her for a year and a half, then helped her get her first clients,” Zander says. Once her friend was out on her own, Zander had a shock: “I heard that she was charging $350 an hour! I was outraged. I wasn’t charging even half that amount! That jolted me—and prompted me to raise my own rates.”

Negotiating for more green is only one possibility. If you’re meeting with your boss, you also could ask for more vacation days or partial tuition to work toward an advanced degree. You could request a loaner laptop or a travel allowance. Or you could decide to spend your out-of-office hours pursuing your passion and getting paid for it. My editor friend Olivia figured out a way to make all the frequent requests for free editing feel less burdensome and end up with money in her pocket. “Recently, an acquaintance asked if I would help her polish the copy on her website. She happens to be a professional organizer, so I said, ‘Let’s do a barter: You help me declutter my apartment and I’ll edit your website.’ Now I have tons of extra closet space and she has great marketing copy.” When former writing students call to see if Olivia will look at their work, she says, “I’m happy to. I charge $125 an hour.” The response? “No one blinks,” she says. “I’m putting the extra cash in a vacation fund.”

How is this advice relevant to me, a freelance writer, or to you, whatever you do? Like many women I know, I have basically taken on any assignment I’ve been offered, even if the pay is cruddy, even if it’s a topic that doesn’t interest me, which is an awfully passive, reactive way to work. Now I’m trying to be more strategic by seeking out ghostwriting opportunities, forcing myself to network and pitching publications and websites I’ve always secretly dreamed of writing for. If I can’t get editors to budge on their per-word rates, I sometimes can persuade them to assign longer stories. Or I can ask an editor to provide time-saving research assistance so I have more hours for the fun part—the actual writing.

I’ll admit, there are moments when asking for all these things makes me sick with nerves. When that happens, I think about the guys I know who are convinced that every word they type is a precious commodity, then I channel their confidence. After all, I’m at least as good as they are. Probably better.

Play to Your Strengths

What do you love? What are you great at? Where do you want to be in 10 years? Being able to answer these questions clearly and confidently will help you get what you deserve.

Forget about being humble. “I have clients make a ‘home runs list’ of all the times they’ve excelled,” says Lauren Zander, cofounder of coaching firm the Handel Group. “The point is to form a strong vision of who you are and how you’re great.”

Do a work-around. A good self-assessment includes writing down what you’re not so good at, too. Then, instead of kicking yourself about your vulnerable areas, work around them. Maybe you’re not the most tech-savvy person in the office but you’re super speedy and solve problems other people can’t. Knowing what you offer—experience, creativity, competence, a knack for teamwork—means you can convincingly argue your worth.

Rally your pals. It’s easier to do scary things like ask for more money when you have some support. After all, there’s nothing like a few encouraging friends to help you maintain a positive, powerful mind-set. So gather your circle around you and have each friend list your marketable assets. (Bribe them with wine and cheese, if necessary!) “It can be thrilling and inspiring to hear exactly what people think you’re terrific at,” author Barbara Stanny says. Their perspective can help you figure out your goals and, just as key, hammer home how much you deserve to achieve them.

Give and take. Maybe you need check-ins with a friend to keep you accountable. Maybe you need tough love. Figure out what works for you, and ask for it. Then turn around and do the same for your friends. Remember: A rising tide lifts all boats. If there are only two women writers out of 20 on the staff of a late-night comedy show, they don’t have as much opportunity to bring in other women. But when a big percentage of the writers are female (as on Mad Men), women gain traction. —M.I.

Try These Tips to Earn More Now

Cast a wide net. “Ask 10 people how much you should be charging—for your baking services, fund-raising skills or your way with words,” Lauren Zander says. “This will help you get used to the idea of monetizing whatever it is you do and the notion that what you offer is worth it.”

Name a specific number. Rather than simply saying, “I’d like to bring in more csh,” figure out exactly what you’d like to earn and what you’ll have to do to make that happen: how many clients you’ll need or cupcakes you’ll have to bake. Setting a specific goal makes it easier to lay out a game plan and actually end up meeting your financial goals.

Talk yourself up. If self-promotion is anathema to you, don’t think of it as selling; think of it as connecting. “I ask my clients to go out and have five meaningful conversations a day about what they do,” Zander says. “Email doesn’t count. To make an endeavor work, you have to put yourself out there and speak from the heart about what you bring to the table.”

Make a vow and keep it. Think about the effort you’re willing to put in (e.g., making five calls to potential clients a day), then promise yourself you’ll do those things, however modest. Give yourself consequences (no reality TV!) if you don’t follow through. Feel free to revise your vows as you go. As Zander says, “You need to keep having new visions of what’s possible.” Then watch your dreams come true. —Paula Derrow